text: In acidic conditions, ptaquiloside gradually undergoes aromatization with the elimination of D-glucose to afford ptaquilosin, and finally pterosin B. Under weakly alkaline conditions, ptaquiloside and its aglycone ptaquilosin are converted into an unstable conjugated dienone intermediate. This ptaquilodienone is the activated form of ptaquiloside and is regarded as the ultimate carcinogen of bracken ferns. Due to the constitution of a cyclopropyl carbinol system, ptaquilodienone is a strong electrophile and acts as a powerful alkylating agent that reacts directly with biological nucleophiles including amino acids, nucleosides, and nucleotides under weakly acidic conditions at room temperature (as shown in the scheme below).